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Jon Hamm, 49, Dating ‘Mad Men’ Guest Star Anna Osceola, 32, 5 Years After Finale
Jon Hamm reportedly has a new woman in his life! The 49-year-old actor is dating Anna Osceola, 32, according to Us Weekly. The mag’s confirmation of this hot new romance comes after the stars were photographed playing tennis together in May. Anna was a guest star on the season finale of Mad Men in 2015, so she briefly shared the screen with Jon on the hit AMC show.